Orange-yellow sulfur dye and process of making same.



UNITED STATES RICHARD GLEY, OF BERLIN, GERM PATENT OFFICE.

ANY, AssIeNoR TO AOTIEN GESELL SCHAFT Ff'R ANILIN FABRIKATION, OF BERLIN, GERMANY. ORANGE-YELLOW SULFUR DYE AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

Patented Feb. 27, 1906.

Application iile d uly 1 1905- Serial No. 268,014

To all whom it may concern.-

Be it known that I, RICHARD GLEY, of S. O. 36 Lohmuhlenstrasse 67, Berlin, in the Kingdom of Prussia, German Empire, have invented new and useful Improvements in the Production of Orange-Yellow Sulfur Dye and Process of Making Same; and I do hereby declare that the following is a full, clear, and exact description of the invention, which will enable others skilled in the art to which it appertains to make and use the same. Mypresent invention relates to the manufacture of yellow to orange-yellow sulfurized dyestuffs and is based on the observation that a mixture of diformyl-meta-toluylenedi amin and para-phenvlenediamin when heated together with sulfur to higher temperatures yields very valuable dyestuffs dyeing unmordanted cotton clear shades which are distinguished by their great fastness. This result is the more surprising, as by heating para-phenylenediamin alone with sulfur one obtains a dyestufl dyeing unmordanted cotton greenish-black shades, (compare German Patent No. 85,330.) Furthermore, the German Patent No. 146,917 would suggest the opinion that a mixture as-used with my -'pres. ent invention would not be a suitable starting product for the production of yellow sulfurized dyestuffs, because in this patent there is usedmeta-toluylenediamin -(i'n combination with 'diformyl-meta-toluylenediamin)-.

that is to say, a substance which contains a methyl group,whereas para-phenylnediamin contains no methyl group and whereas it, was the general opinion that such-a methyl group would be an essential feature for the formation of such sulfur dyestuffs as thepresent invention relates to.- 1

i In carryingout my present inventionI proceed as follows, the parts being by weight: forty parts of sulfur, 6.4 parts of para-phenylenediamin, and nine parts of diformylmeta-toluylenediamin,this being-obtained by the action of formic acid on meta-toluylenediamin, are melted together. Then the temperature is gradually-raised to 250 and this temperature maintained till the evolution of sulfurted hydrogen has totally ceased. The melt after cooling is finely pulverized or a ground. There results thereby a brown-red powder, insoluble in water and alcohol soluble in which solution is yellow shades, showing a full hand milling. 1

from the scope of my invention.

partin Ior instance, I state that a somewhat Thus,

dish tints, whereas heating to a temperature ives a product dyeing more yellowish tints. Iurthermore, the proportions of the ingredients may also e varied within good without essentially changing the result Now what I claim is- 1. The manufacture of a new, sulfurized meta-toluylenedialnin and para-phenylene diamin with sulfur to above 200 centigradc.

2. The new sulf'urized dyestufl' obtained by the action of sulfur on a' nixture of diformyl-meta-toluylenediamin and paraphe- RICHARD GLEY. Witnesses:

HENRY HASPER, GUST V 'L ronr soda-lye with a yellow coloration,

precipitated by the addition of hydrochloric acid in yellowbrown The dyestufl' dissolves in sodium sulfid with a yellow coloration and dyes from such a solution, especially when added with common salt, unmordanted cotton clear orangesight overand a great fastness to washing and It is obvious to those skilled in the art that' I am not limited to the above example nor to the details given therein, and many variations'may be made with the process as defined in the foregoing example without dehigher temperature at which the melt is effected will yield a product dyeing more redlimits nylenediamin, being, when well pulverized or lower than that mentioned in the example 8e dyestuff, by heatiilg a mixture of diformyl- 

